WO2014030845A1 - Composition pour revêtement dur - Google Patents

Composition pour revêtement dur Download PDF

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Publication number
WO2014030845A1
WO2014030845A1 PCT/KR2013/006773 KR2013006773W WO2014030845A1 WO 2014030845 A1 WO2014030845 A1 WO 2014030845A1 KR 2013006773 W KR2013006773 W KR 2013006773W WO 2014030845 A1 WO2014030845 A1 WO 2014030845A1
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WO
WIPO (PCT)
Prior art keywords
hard coating
coating composition
photocurable
photoinitiator
present
Prior art date
Application number
PCT/KR2013/006773
Other languages
English (en)
Korean (ko)
Inventor
강준구
장영래
홍성돈
정순화
허은규
Original Assignee
주식회사 엘지화학
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Filing date
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Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP13831327.5A priority Critical patent/EP2873699A4/fr
Priority to US14/423,420 priority patent/US10000655B2/en
Priority to CN201380055267.4A priority patent/CN104736633A/zh
Priority to JP2015528383A priority patent/JP2015531021A/ja
Publication of WO2014030845A1 publication Critical patent/WO2014030845A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/16—Cyclodextrin; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D135/02—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2433/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/16—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the structure of the carrier layer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24917—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including metal layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/269—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension including synthetic resin or polymer layer or component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848—Three or more layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]

Definitions

  • the present invention relates to a hard coating composition. More specifically, the present invention relates to a hard coat composition capable of forming a hard coat film exhibiting excellent impact resistance and optical properties.
  • Glass or tempered glass is generally used as a material having excellent mechanical properties in the display window or the front plate of the mobile device.
  • the glass causes the mobile device to become heavier due to its own weight, and there is a problem of breakage due to an external stratification.
  • Plastic resin is being researched as a substitute material for glass.
  • Plastic resin compositions are suitable for the trend toward a lighter mobile device because they are lightweight and less prone to breakage.
  • compositions have been proposed for coating a hard coat layer on a support substrate to achieve compositions having high hardness and wear resistance properties.
  • a method of increasing the thickness of the hard coating layer may be considered.
  • the surface hardness may be increased.
  • the wrinkles and curls increase due to the hardening shrinkage of the hard coating layer, cracking or peeling of the hard coating layer tends to occur. Not easy ' In recent years, several methods have been proposed to achieve high hardness of the hard coat film and to solve the problem of curling due to cracking and curing shrinkage of the hard coat filling.
  • Korean Unexamined Patent Publication No. 2010-0041992 discloses a hard coating composition excluding a monomer and using a binder resin including an ultraviolet curable polyurethane acrylate based oligomer.
  • the hard coating composition disclosed above is not strong enough to replace the glass panel of the display with a pencil hardness of about 3H.
  • the present invention provides a hard coating composition capable of forming a hard coating film having excellent layer resistance and optical properties.
  • It provides a hard coating composition comprising an organic solvent.
  • a hard coating composition in the form of a solvent (solvent-free) comprising a photoinitiator.
  • the hard coating composition of the present invention can be used to prepare a hard coating film exhibiting impact resistance, scratch resistance, and high transparency and having excellent processability. Accordingly, the hard coating film formed by using the hard coating composition of the present invention exhibits impact resistance, scratch resistance, and high transparency to cover touch panels of mobile communication terminals, smartphones or tablet PCs, and various displays. It can be used to replace glass in a substrate or device substrate.
  • first and second are used to describe various components, which terms are used only for the purpose of distinguishing one component from other components.
  • each component is referred to as being formed "on” or “on” of each component, it means that each component is directly formed on each component, or other components are each It can be formed additionally between the layer, the object, the substrate.
  • 1 to 6 functional acrylate monomers; Photocurable elastomers; Photoinitiator; And organic solvents It provides a hard coating composition.
  • the acrylate-based means not only acrylate but also methacrylate, or a derivative in which a substituent is introduced into acrylate or methacrylate.
  • the 1 to 6 functional acrylate monomers include, for example, hydroxyethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA), nucleic acid dididiacrylate (HDDA), tripropylene glycol diacrylate (TPGDA). ), Ethylene glycol diacrylate (EGDA), trimethyl to propane triacrylate (TMPTA), trimethylolpropane ethoxy triacrylate (TMPEOTA), glycerin propoxylated triacrylate (GPTA) : The nucleate acrylate (DPHA) etc. are mentioned for a latex (PETA) or dipentaerythrite.
  • the 1 to 6 functional acrylate monomers may be used alone or in combination with each other.
  • the 1 to 6 functional acrylate monomers are based on 100 parts by weight of solids including the 1 to 6 functional acrylate monomers, the photocurable elastomer, and the photoinitiator. About 20 to about 79.5 parts by weight, or about 20 to about 49.5 parts by weight.
  • the 1 to 6 functional acrylate monomer is in the above range, it is possible to form a hard coat film having good physical properties such as high hardness and scratch resistance.
  • the hard coating composition of the present invention includes a photocurable elastomer ⁇
  • the photocurable elastomer means a polymer material that exhibits elasticity and includes a functional group capable of crosslinking polymerization by ultraviolet irradiation.
  • the photocurable elastomer is at least about 15%, for example from about 15 to about 200%, or from about 20 to about 200%, or from about 20 to about as measured by ASTM D638. It can have an elongation of 150%.
  • the photocurable elastomer is cross-polymerized with the 1 to 6 functional acrylate monomer to form a hard coat layer after curing is formed Flexibility and impact resistance can be imparted to the hard coat layer.
  • the weight ratio of 1 to 6 functional acrylate based monomers may be about 20:80 to about 80:20 or about 20:80 to about 50:50.
  • the hard coat film having good physical properties may be formed without degrading optical properties while exhibiting excellent layer resistance.
  • the photocurable elastomer may be a polymer or oligomer having a weight average molecular weight in the range of about 1,000 to about 600,000 g / mol, or about 10,000 to about 600,000 g / mol.
  • the photocurable elastomer may be, for example, at least one member selected from the group consisting of polycaprolactone, urethane acrylate polymer, and polyrotaxane.
  • polycaprolactone is formed by ring-opening polymerization of caprolactone and has excellent physical properties such as flexibility, layer resistance, and durability.
  • the urethane acrylate polymer has excellent elasticity and durability, including urethane bonds.
  • the polyrotaxane refers to a compound in which a dumbbell shaped molecule and a cyclic compound are structurally fitted.
  • the dumbbell-shaped molecule includes a constant linear molecule and a blocking group disposed at both ends of the linear molecule, the linear molecule penetrates the inside of the cyclic compound, and the cyclic compound moves along the linear molecule. Can be prevented from being separated by the blocker.
  • a cyclic compound bonded to a lactone compound having a (meth) acrylate compound introduced at the terminal; Linear molecules penetrating the cyclic compound; And a rotasein compound disposed at both ends of the linear molecule and including a blocking group to prevent the cyclic compound from being separated.
  • the cyclic compound may penetrate or surround the linear molecule. It may be used without any limitation as long as it has a degree of degree, and may include functional groups such as hydroxyl, amino, carboxyl, thiol or aldehyde groups that can be reacted with other polymers or compounds. Specific examples of such cyclic compounds include ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, or a combination thereof.
  • a compound having a straight chain form having a molecular weight of a predetermined or more may be used without great limitation, but a polyalkylene compound or a polylactone compound may be used.
  • a polyoxyalkylene compound containing an oxyalkylene repeating unit having 1 to 8 carbon atoms or a polylactone compound having a lacron repeating unit having 3 to 10 carbon atoms may be used.
  • the containment group is manufactured. It can be appropriately adjusted according to the properties of the rotasein compound, for example selected from the group consisting of dinitrophenyl group, cyclodextrin group, ammantane group, triyl group, fluorescein group and pyrene group
  • Such polyrotaxane compounds may have excellent scratch resistance and may exhibit self-healing ability when scratches or external damages occur.
  • the hard coating composition of the present invention by providing a photocurable elastic polymer to photo-curing to impart high hardness and flexibility to the hard coating layer, in particular, it is possible to prevent damage by the outer layer lattice to ensure excellent layer resistance.
  • the photocurable elastomer is about 20 to about 79.5 based on 100 parts by weight of the solid containing the 1 to 6 functional acrylate-based monomer, the photocurable elastomer, and the photoinitiator Or from about 20 to about 49.5 parts by weight.
  • the content of the photocurable elastomer is too high out of the weight ratio, the physical properties of the hard coat layer may be deteriorated, such as the occurrence of curl after curing or the scratch resistance decreases.
  • the content of the photocurable elastomer is too small, it may not be able to achieve the layer resistance sufficiently.
  • the hard coating composition of the present invention includes a photoinitiator.
  • 1-hydroxy-cyclonucleosil-phenyl ketone 2-hydroxy-2-methyl-1-phenyl-1-propane, 2-hydroxy-1- [4_ (2-Hydroxyethoxy) phenyl] -2-methyl-1-propanone, methylbenzoylformate, ⁇ , ⁇ -dimethoxy- ⁇ _phenylacetophenone, 2-benzoyl-2- (dimethylamino ) -1- [4- (4-morpholinyl) phenyl] -1-butanone, 2-methyl-1- [4- (methylthio) phenyl] -2- (4-morpholinyl) -1 -Propanone diphenyl (2,4,6-trimethylbenzoyl) -phosphine oxide, or bis (2,4,6-trimethylbenzoyl)-phenylphosphine oxide, and the like, but are not limited thereto.
  • Irgacure 184 Commercially available products include Irgacure 184, Irgacure 500, Irgacure 651, Irgacure 369, Irgacure 907, Darocur 1173, Darocur MBF, Irgacure 819, Darocur TPO, Irgacure 907, and Esacure KIP 100F.
  • These photoinitiators can be used individually or in mixture of 2 or more types different from each other.
  • the photoinitiator is about 0.5 to about 10 weights based on 100 parts by weight of solids including the 1 to 6 functional acrylate-based monomer, the photocurable elastomer, and the photoinitiator. Parts, or about 1 to about 5. parts by weight.
  • the photoinitiator is in the above range, the crosslinked photopolymerization can be achieved without lowering the physical properties of the hard coat film.
  • the hard coating composition of the present invention comprises an organic solvent.
  • the organic solvent is methane, ethane, an alcoholic solvent such as isopropyl alcohol, butanol, 2-methoxyethane, 2-ethoxyethane, 1-methoxy-2.
  • Alkoxy alcohol solvents such as propane, acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl propyl ketone, ketone solvents such as cyclonucleanone, propylene glycol monopropyl ether, propylene glycol monomethyl ether, ethylene glycol monoethyl ether , Ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethyl glycol monoethyl ether, diethyl glycol monopropyl ether, diethyl glycol monobutyl ether, diethylene glycol-2-ethyl nucleosil ether Ether solvents such as, aromatic solvent
  • the content of the organic solvent is not particularly limited because it can be variously adjusted within a range that does not lower the physical properties of the hard coating composition of the present invention, the 1 to 6 functional
  • the weight ratio of solids to organic solvents may be included in a range of about 70:30 to about 99: 1 based on 100 parts by weight of the solid content including the acrylate monomer, the photocurable elastomer, and the photoinitiator.
  • the hard coating composition of the present invention in addition to the above-mentioned 1 to 6 functional acrylate monomer, photocurable elastomer, photoinitiator and organic solvent, the present invention, such as surfactant, anti-yellowing agent, leveling agent, antifouling agent It may further include an additive commonly used in the field.
  • the content can be variously adjusted within a range that does not lower the physical properties of the hard coating composition of the present invention, it is not particularly limited, for example, with respect to 100 parts by weight of the hard coating composition, about 0.1 to about 10 parts by weight May be included.
  • the hard coating composition may include a surfactant as an additive, and the surfactant may be a 1 to 2 functional fluorine acrylate, a fluorine surfactant or a silicone surfactant.
  • the surfactant may be included in the form of being dispersed or crosslinked in the crosslinked copolymer.
  • the additive may include a yellowing inhibitor
  • the yellowing inhibitor may include a benzophenone compound or a benzotriazole compound.
  • the viscosity of the hard coating composition is not particularly limited as long as it has a suitable flowability and coating property, but may exhibit a relatively high viscosity.
  • the hard coating composition of the present invention has a viscosity of about 100 to about 1,200 cps, or about 100 to about 1,200 cps, or about 150 to about 1,200 cps, or about 300 to about 1,200 cps at a temperature of 25 ° C. It may have a viscosity.
  • a solvent-free comprising a 1 to 6 functional acrylate-based monomer, a photocurable elastomer, and a photoinitiator It provides a hard coating composition in the form.
  • the solvent-free hard coating composition does not include an organic solvent may exhibit a higher viscosity.
  • the hard coating composition of the present invention may have a viscosity of about 300 to about 1,200 cps, or about 300 to about 1,200 cps, or about 500 to about 1,200 cps, or about 800 to about 1,200 cps at a temperature of 25 ° C. It may have a viscosity.
  • the hard coating composition of the present invention comprising the above-described components can form a hard coating layer by applying a support substrate to the photocuring. .
  • the support substrate to which the hard coating composition of the present invention is applied can be used without particular limitation in the production method or material of the support substrate such as a stretched film or a non-stretched film as long as it is a transparent plastic resin.
  • the supporting substrate may be a polyester such as polyethylene terephthalate (PET), a polyethylene such as ethylene vinyl acetate (EVA), a cyclic olefin polymer (cyclic olefin polymer) , COP), cyclic olefin copolymer (COC), polyacrylate (PAC), polycarbonate (PC), polyethylene (PE), polymethyl methacrylate (polymethylmethacrylate, PMMA) ), Polyetheretherketon (PEEK), polyethylenenaphthalate (PEN), polyetherimide (PEI), polyimide (PI), triacetylcellulose (TAC), MMA (methyl methacrylate), or a film containing a fluorine resin or the like.
  • the support substrate may be
  • the support substrate is a substrate having a multilayer structure of polyethylene terephthalate (PET), It can be a substrate having a structure of two or more layers formed by coextrusion of polymethyl methacrylate (PMMA) / polycarbonate (PC).
  • PET polyethylene terephthalate
  • PMMA polymethyl methacrylate
  • PC polycarbonate
  • the support substrate may be a substrate including a copolymer of polymethylmethacrylate (PMMA) and polycarbonate (PC).
  • PMMA polymethylmethacrylate
  • PC polycarbonate
  • the thickness of the support substrate is not particularly limited, but a support substrate having a thickness of about 30 to about 1,200 / ⁇ , or about 50 to about 800 may be used.
  • the thickness of about 50 or more for example about 50 to about 300 / ⁇ , or about 50 to about 200 /, or about 50 to about 150, Or a hard coat layer having a thickness of about 70 to about 150 microns.
  • the hard coating layer formed using the hard coating composition according to the present invention in particular, when the impact is applied from the outside can be given to the excellent impact resistance to the hard coating film.
  • the hard coat layer may be formed by a conventional method used in the art.
  • the hard coating composition according to the present invention is applied to one surface of a support substrate.
  • the method of applying the composition is not particularly limited as long as it can be used in the technical field to which the present technology belongs, for example, bar coating method, knife coating method, coating method, blade coating method, die coating method, micro gravure coating Method, comma coating method, slot die coating method, lip coating method, or solution casting method.
  • the hard coat layer may be formed by irradiating ultraviolet light on the applied hard coat composition.
  • the hard coating composition of the present invention As described above it can form a hard coating layer excellent in impact resistance.
  • the hard coat layer using the hard coat composition of the present invention may be formed on the other side of the support substrate on which the other hard coat layer is formed.
  • the film including the hard coating layer formed using the hard coating composition of the present invention exhibits excellent high hardness, layer resistance, scratch resistance, high transparency, durability, light resistance, high transmittance, etc., and thus may be usefully used in various fields.
  • the film including the hard coating layer formed by using the hard coating composition of the present invention may have excellent layer resistance to replace the glass.
  • the film including the hard coating layer formed using the hard coating composition of the present invention may not generate cracks when the 22 g iron ball is repeatedly dropped freely 10 times at a height of 50 cm.
  • the hard coating layer formed by using the hard coating composition of the present invention when the steel wool (0000) is mounted on a friction tester (steel wool) # 0000 after reciprocating 400 times with a load of 500g may occur less than two scratches Can be.
  • the hard coating layer formed using the hard coating composition of the present invention may be 91.0% or more, or 92.0% or more, haze 1.0% or less, or 0.5% or less, or 4% or less.
  • the hard coating layer formed using the hard coating composition of the present invention may be 1.0 or less.
  • the difference between the initial color b value and the color b value after 72 hours or more exposure to an ultraviolet lamp in the UVB wavelength region may be 0.5 or less, or 0.4 or less.
  • the hard coating layer formed by using the hard coating composition of the present invention when exposed to a flat surface after 70 hours or more at a temperature of 50 ° C or more and a humidity of 80% or more, each corner or one of the hard coating film
  • the maximum value of the distance away from the transition plane may be about 1.0 mm or less, or about 0.6 mm or less, or about 0.3 mm or less. More specifically, when placed in a plane after exposure for 70 to 100 hours at a temperature of 50 to 90 ° C and a humidity of 80 to 90%, the maximum of the distance of each corner or one side of the hard-coating film in the plane The value may be about 1.0 mm or less, or about 0.6 mm or less, or about 0.3 mm or less.
  • the hard coating layer formed using the hard coating composition of the present invention exhibits high hardness, layer resistance, scratch resistance, high transparency, durability, light resistance, and high transmittance, and thus may be usefully used in various fields.
  • mobile It can be used for a touch panel of a terminal, a smartphone or a tablet PC, and a cover substrate or an element substrate of various displays.
  • the weight average molecular weight of the obtained polyrotasein was 600,000 g / mol, and elongation measured by ASTM D638 was 20%.
  • Example 1 The weight average molecular weight of the obtained polyrotasein was 600,000 g / mol, and elongation measured by ASTM D638 was 20%.
  • TMPTA trimethylolpropane triacrylate
  • POPTA polyrotasein of Preparation Example 1
  • photoinitiator trade name: Darocur TPO
  • benzotriazole yellowing inhibitor trade name: Tinuvin 400
  • O.lg fluorine-based surfactant
  • FC4430 fluorine-based surfactant
  • Methyl ethyl ketone lg was mixed to prepare a first hard coat composition.
  • HSA Hydroxyethyl acrylate 2g
  • the particle diameter is 20-30nm nano silica is 40 parts by weight 0/0 dispersed silica-dipentaerythritol hex the EPO Li acrylate (DPHA) complex 8g (silica 3.2g, DPHA 4.8g) , 0.2 g of a photo-initiated crab (trade name: Darocur TPO), a banjo triazole-based yellowing inhibitor (trade name: Tinuvin 400) O.lg, and 0.05 g of a fluorine-based surfactant (trade name: FC4430) were mixed to prepare a second hard coating composition.
  • the second hard coat composition was applied onto a PET support substrate having a thickness of 15 cm X 20 cm, 188.
  • the first photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • the first hard coating composition was applied to the back side of the supporting substrate.
  • a second photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp to prepare a hard coat film.
  • the thicknesses of the first and second hard coat layers formed on both sides of the resin were 100 respectively.
  • Example 3 In the first hard coating composition, 4 g of urethane acrylate polymer (trade name: UA200PA, Shinnakamura Chemical, weight average molecular weight 2,600 g / mol, elongation at 170% according to ASTM D638) was used instead of 4 g of polyrotacein of Preparation Example 1. Except that a hard coat film was prepared in the same manner as in Example 1.
  • urethane acrylate polymer trade name: UA200PA, Shinnakamura Chemical, weight average molecular weight 2,600 g / mol, elongation at 170% according to ASTM D638
  • Example 4 In the first hard coating composition, 4 g of urethane acrylate-based polymer (trade name: UA340P, Shinnakamura Chemical, weight average molecular weight 13,000 g / mol, elongation according to ASTM D638) was used instead of 4 g of polyrotasein of Preparation Example 1. Except that a hard coat film was prepared in the same manner as in Example 1.
  • urethane acrylate-based polymer trade name: UA340P, Shinnakamura Chemical, weight average molecular weight 13,000 g / mol, elongation according to ASTM D638
  • Example 5 After the curing was completed in Example 1, except that the thickness of the first and second hard coat layer formed on both sides of the resin to 150, respectively, a hard coat film was prepared in the same manner as in Example 1.
  • Example 6 After the curing was completed in Example 1, except that the thickness of the first and second hard coat layer formed on both sides of the resin to 150, respectively, a hard coat film was prepared in the same manner as in Example 1.
  • TMPTA trimethylolpropane triacrylate
  • POPTA polyrotasein of Preparation Example 1
  • photoinitiator trade name: Darocur TPO
  • benzotriazole yellowing inhibitor trade name: Tinuvin 400
  • FC4430 fluorine-based surfactant
  • HSA Hydroxyethyl acrylate 2g
  • the particle diameter is 20-30nm nano silica is 40 parts by weight 0/0 dispersed silica-dipentaerythritol hex the EPO Li acrylate (DPHA) complex 8g (silica 3.2g, DPHA 4.8g) 0.2 g of a photoinitiator (trade name: Darocur TPO), a benzotriazole-based yellowing inhibitor (trade name: Tinuvin 400) O.lg, and 0.05 g of a fluorine-based surfactant (trade name: FC4430) were mixed to prepare a second hard coating composition.
  • DPHA dispersed silica-dipentaerythritol hex the EPO Li acrylate
  • DPHA dispersed silica-dipentaerythritol hex the EPO Li acrylate (DPHA) complex 8g (silica 3.2g, DPHA 4.8g) 0.2 g of
  • the second hard coat composition was applied onto a PET support substrate having a thickness of 15 cm X 20 cm, 188.
  • the first photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • the first hard coating composition was applied to the back side of the supporting substrate.
  • a second photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp to prepare a hard coat film.
  • the thickness of the first hard coat layer was 125 and the thickness of the second hard coat layer was 100 / im. Comparative Example 1
  • the second hardcoat composition of Example 1 was applied onto a PET support substrate having a thickness of 15 cm X 20 cm, 188 ⁇ .
  • the first photocuring was carried out by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • Example 2 The second hard coating composition of Example 1 was applied to the back side of the supporting substrate. Next, ultraviolet rays having a wavelength of 280-350 nm were irradiated using a black light fluorescent lamp. Irradiation was performed to perform a second photocuring to prepare a hard coat film. After curing was completed, the thicknesses of the hard coat layers formed on both sides of the resin were each 100. Comparative Example 2
  • TMPTA trimethyl propane triacrylate
  • photoinitiator trade name:
  • Darocur TPO 0.2 g
  • benzotriazole yellowing inhibitor trade name: Tinuvin 400
  • fluorine-based surfactant trade name: FC4430
  • methyl ethyl ketone lg was mixed to prepare a first hard coating composition.
  • Example 1 The second hard coat composition and the remaining process was the same as in Example 1 to prepare a hard coat film.
  • Example 1 to 6 and Comparative Examples 1 and 2 the components and contents of the first and second hard coating compositions are summarized in Table 1 below.
  • Each hard coat film was wound on a cylindrical lteltel having a diameter of lcm with the first hard coat layer outward, and then cracks were judged to determine whether or not cracks occurred, 0K and X when cracks occurred.
  • Comparative Examples 1 and 2 in which the first hard coat layer does not include a photocurable crosslinked copolymer of 1 to 6 functional acrylate monomers and a photocurable elastomer, have no stratified layer resistance.

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  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
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  • Paints Or Removers (AREA)
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Abstract

La présente invention concerne une composition pour revêtement dur, et plus spécifiquement une composition pour revêtement dur qui puisse former un film de revêtement dur présentant une résistance au choc et des propriétés supérieures. La présente invention concerne un film de revêtement dur présentant une résistance au choc, une résistance aux éraflures, une transparence élevée et une aptitude au traitement supérieure.
PCT/KR2013/006773 2012-08-23 2013-07-29 Composition pour revêtement dur WO2014030845A1 (fr)

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EP13831327.5A EP2873699A4 (fr) 2012-08-23 2013-07-29 Composition pour revêtement dur
US14/423,420 US10000655B2 (en) 2012-08-23 2013-07-29 Hard coating composition
CN201380055267.4A CN104736633A (zh) 2012-08-23 2013-07-29 硬涂料组合物
JP2015528383A JP2015531021A (ja) 2012-08-23 2013-07-29 ハードコーティング組成物

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KR20120092529 2012-08-23
KR10-2012-0092529 2012-08-23
KR10-2013-0089102 2013-07-26
KR1020130089102A KR101415838B1 (ko) 2012-08-23 2013-07-26 하드코팅 조성물

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JP2015533675A (ja) 2015-11-26
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US10000655B2 (en) 2018-06-19
US20150299505A1 (en) 2015-10-22
TW201634277A (zh) 2016-10-01
KR101470465B1 (ko) 2014-12-08
EP2873694A1 (fr) 2015-05-20
US20150225598A1 (en) 2015-08-13
CN104736633A (zh) 2015-06-24
EP2873699A4 (fr) 2016-05-04
EP2873699A1 (fr) 2015-05-20
TWI558555B (zh) 2016-11-21
KR20140027022A (ko) 2014-03-06
CN104736615B (zh) 2017-09-26
JP6276764B2 (ja) 2018-02-07
TWI635955B (zh) 2018-09-21
TW201420337A (zh) 2014-06-01
WO2014030846A1 (fr) 2014-02-27
US9909026B2 (en) 2018-03-06
TWI577760B (zh) 2017-04-11
KR20140027023A (ko) 2014-03-06
TW201422734A (zh) 2014-06-16
EP2873694A4 (fr) 2016-04-13

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